A New α-Amino Acid γ-Anion Equivalent: Direct Synthesis of Enantiomercially  Pure Protected Amino Acids

Richard F. W. Jackson; Neil Wishart; Martin J. Wythes

doi:10.1055/s-1993-22409

Synlett 1993; 1993(3): 219-220
DOI: 10.1055/s-1993-22409

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A New α-Amino Acid γ-Anion Equivalent: Direct Synthesis of Enantiomercially Pure Protected Amino Acids

Richard F. W. Jackson^* , Neil Wishart, Martin J. Wythes

^*Department of Chemistry, Bedson Building, The University of Newcastle, Newcastle upon Tyne, NE1 7RU, England

Abstract

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Treatment of the glutamic acid derived iodide 7 with Rieke copper at -78 °C generates the functionalised alkyl copper reagent 6b an α-amino acid γ-anion equivalent, which reacts directly with acid chlorides and allylic chlorides at -30 °C to give the products of substitution 10-12. In two cases, the enantiomeric purity of the products was established by comparison of optical rotation data with literature values, indicating that the coupling process occurs without racemisation.

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